Triphosgene → (2R,4S)-5-biphenyl-4-yl-4-isocyanato-2-methyl-pentanoic acid benzyl ester

HRID 1469606Notes

Reaction equation

HRID 1469606 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.Cl.[CH2:14]([O:21][C:22](=[O:41])[C@H:23]([CH3:40])[CH2:24][C@H:25]([NH2:39])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[CH2:14]([O:21][C:22](=[O:41])[C@H:23]([CH3:40])[CH2:24][C@H:25]([N:39]=[C:2]=[O:4])[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:31][CH:32]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 67505899HCID 67505899, compound

Product 1

HCID 86648208(2R,4S)-5-biphenyl-4-yl-4-isocyanato-2-methyl-pentanoic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred 1:1 mixture of methylene chloride/8% aqueous NaHCO3 (6 mL) at 0° C. is added triphosgene (18 mg, 0.061 mmol). After stirring the mixture at 0° C. for 5 minutes, (2R,4S)-4-amino-5-biphenyl-4-yl-2-methyl-pentanoic acid benzyl ester hydrochloride (75 mg, 0.183 mmol) is added and stirring is continued for 15 minutes. The organic phase is separated and dried over sodium sulfate. The solvent is removed under reduced pressure to furnish (2R,4S)-5-biphenyl-4-yl-4-isocyanato-2-methyl-pentanoic acid benzyl ester.

Workup

  1. stirringAfter stirring the mixture at 0° C. for 5 minutes
  2. stirringstirring
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-fc35a970a275426283b2852f1a53f9c2
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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